Heterogeneous solid catalysis by the commercially available perfluorosulfonic ionomer Aquivion-H allowed 1,2:5,6-diacetonide of D-mannitol (1), immediate precursor of important unichiral C3-synthons, to be efficiently obtained from D-mannitol and 2,2-dimethoxypropane in DMF at room temperature. The 1,2-monoacetonide, whose intermediate formation is the rate-limiting step, could be almost completely converted into 1 with limited concurrent transformation of 1 into triacetonides. In line with recent literature reports, these results indicate that heterogeneous catalysis by Aquivion-H surpasses the performances of homogeneous acidic catalysis assuring, presumably for its peculiar morphology, a higher product selectivity. Easy recovery at the end of the reaction and recyclability are additional advantages of this solid acid catalyst.

Efficient conversion of d-mannitol into 1,2:5,6-diacetonide with Aquivion-H as a recyclable catalyst / C. Bolchi, R. Appiani, G. Roda, V. Bertolini, S. Arnoldi, M. Pallavicini. - In: CARBOHYDRATE RESEARCH. - ISSN 0008-6215. - 499:(2021), pp. 108229.1-108229.4. [10.1016/j.carres.2020.108229]

Efficient conversion of d-mannitol into 1,2:5,6-diacetonide with Aquivion-H as a recyclable catalyst

C. Bolchi
Primo
Supervision
;
R. Appiani
Secondo
;
G. Roda;V. Bertolini;S. Arnoldi
Penultimo
;
M. Pallavicini
Ultimo
2021

Abstract

Heterogeneous solid catalysis by the commercially available perfluorosulfonic ionomer Aquivion-H allowed 1,2:5,6-diacetonide of D-mannitol (1), immediate precursor of important unichiral C3-synthons, to be efficiently obtained from D-mannitol and 2,2-dimethoxypropane in DMF at room temperature. The 1,2-monoacetonide, whose intermediate formation is the rate-limiting step, could be almost completely converted into 1 with limited concurrent transformation of 1 into triacetonides. In line with recent literature reports, these results indicate that heterogeneous catalysis by Aquivion-H surpasses the performances of homogeneous acidic catalysis assuring, presumably for its peculiar morphology, a higher product selectivity. Easy recovery at the end of the reaction and recyclability are additional advantages of this solid acid catalyst.
D-mannitol; Aquivion-H; 1,2:5,6-di-O-Isopropylidene-D-mannitol; 2,2-Dimethoxypropane; Acetonides
Settore CHIM/06 - Chimica Organica
Settore CHIM/08 - Chimica Farmaceutica
2021
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/806801
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